A bitter pill wrapped in a sweet cherry coating, comic Natasha Leggero is a double threat of intoxicating charm and tabloid cruelty. With her Audrey Hepburn style and merciless observational humor, she's known to raise the I-can't-believe-she-just-said-that bar during her regular appearances on Chelsea Lately, while still maintaining an authenticity that transcends shock for shock's sake. In anticipation of her upcoming shows at Comedy Works, we chatted with Leggero about her sweet-and-sour persona, white-trash fights on her Facebook page, and why male comedians dress like shit.

Josiah Hesse: I assume that, for some people, it comes as a surprise that your comedy has the ability to be so relentlessly cruel, since you initially come off as very sweet and pretty. Is that something you were aware of when beginning as a standup?

Natasha Leggero: That's interesting. I know that's true for someone like Sarah Silverman -- she's so cute, and then she says those things. It's a common thing in standup, but it certainly wasn't intentional. I've always had a mean streak and been sarcastic. Now I just let it live on stage, but it used to be my entire personality. On the stage you can let this part of you out, a part that maybe you've outgrown but it's still entertaining.

How do you balance out being very cruel in the content of your performance while still maintaining charm and likability?

It's called talent, darling. I don't really know how to explain it. I'll tell you this: I studied theater criticism in college -- and when I developed this critical side of me, I would get praised for it. I grew up in the theater as a child, so when I went to Broadway I could write these scathing reviews of things that I hated, and to my surprise, my teachers were really into it. I had trained my mind to do that, and when I went to L.A. I just started directing it toward my surroundings and talking about things that were happening here.

It's interesting that you would use the same faculties for standup as you would theater criticism, considering that academics and many intellectuals would consider one more prestigious than the other.

Exactly. But I talk about toilet babies, so...

But, yeah, I think most of the people who really respect comedy are other comedians, because they take it seriously and consider it an art form. They craft their jokes, and they philosophize about standup with other comics. The people who do it are very passionate and serious about it.

You have an astounding fashion sense, which is unusual for a standup comic. Why is it that so many comics today have this anti-fashion, Seattle-in-the-'90s "realness" about them?

I think there's something bad happening right now where every man dresses like shit. Not quite every man, but it seems like you look around and everyone started dressing like shit. I don't know what the motive is there, but it doesn't age well. You don't want to be a 35-year-old in dirty Converse and a sweatshirt.

I've always felt that you want to dress a little better than the people you're performing for. When I first started standup, someone said, "If you dress like the audience, you become one of them."

I feel like that's part of the reason someone like Russell Brand isn't respected as a standup in the U.S. They want dressed-down, average-looking people like Louis C.K. and David Cross.

Russell Brand has a lot of material about how bad America is, in a pretty edgy way, and I don't think people like that.

Many people know you as a very urban comic who comments on celebrity culture, but you grew up in a small town in the Midwest. Do you think this gave you a different outlook than standups from New York or L.A.?

Oh, definitely. You're a little less sophisticated, so you have to try a little harder. Maybe not as much today because of the Internet, but when I was growing up, we weren't the first people to get trends. We didn't get sushi in Rockford until, like, 2004. It does help create a character a bit: You really have to come up with your own entertainment; you have to seek out cool music and artists. But I'm glad I grew up in the Midwest.

In your standup, you talk about not wanting to add your family on Facebook, which illustrates the differences between where you grew up and the world you're in now. Is that something you continue to deal with?

I don't really go onto Facebook very much anymore. I feel like whenever I do it's like this bad, white-trash Christmas party is about to break out on my page. My brother will be like, "Fuck you, Dad," and my mom will "like" it. It's weird how people in their thirties refer to where their parents live as "home." I'm making my own home.

And that home of yours is somewhat engrossed in the celebrity world, or at least commenting on it. Do you feel that nothing is off limits when poking fun at famous people?

That's a hard question. It's hard to say who deserves what. Some people who are having a really hard time in the media you want to leave alone, especially if they're really young and have addiction problems. But some people I do regard as human pollution, and what they do is a form of pollution, so I don't have a hard time bringing that to people's attention.

Audiences love you for that, which makes me assume that they'd been thinking the same thing but maybe couldn't vocalize it as well as you do.

Well, as a comic, that's what you do.You bring things to people's attention -- in anything. It doesn't have to be about celebrities; it could be something that happened at the grocery store, and people are like, "Oh, that happened to me, too!" You want to make people think about things that they can relate to but maybe had never thought of.

I had that same experience watching your standup recently, when you said that you never planned to have children. It made me think about how that decision is offensive to some people, and I wondered why that is.

What I said was, "I'll never be pregnant...for long." I might get some Asian woman to carry my baby. If there's an option to not carry my baby, I would do it. I mean, I'd hang out with my surrogate.

But do you think there are a lot of people, perhaps from where you grew up, that are offended by a woman refusing to carry a child?

Oh, yeah. A friend of mine from Rockford has thirteen kids, and I'm like, "It's a birth canal, not Soul Train."

Natasha Leggero will perform at 8 p.m., Thursday, April 8, with two more shows on Friday, and another two on Saturday, at Comedy Works, 1226 15th Street. Tickets are $17-$25. For more information, visit comedyworks.com.